DE102011107959A1 - Herstellung von optisch reinem Propan-1,2-diol - Google Patents

Herstellung von optisch reinem Propan-1,2-diol Download PDF

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Publication number
DE102011107959A1
DE102011107959A1 DE102011107959A DE102011107959A DE102011107959A1 DE 102011107959 A1 DE102011107959 A1 DE 102011107959A1 DE 102011107959 A DE102011107959 A DE 102011107959A DE 102011107959 A DE102011107959 A DE 102011107959A DE 102011107959 A1 DE102011107959 A1 DE 102011107959A1
Authority
DE
Germany
Prior art keywords
diol
heterogeneous catalysis
carried out
propane
lactide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
DE102011107959A
Other languages
German (de)
English (en)
Inventor
Wolfgang Tietz
Dr. Schulze Joachim
Prof. Dr. Börner Armin
Prof. Dr. Kühlein Klaus
Dr. Shuklov Ivan
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ThyssenKrupp Industrial Solutions AG
Original Assignee
ThyssenKrupp Uhde GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ThyssenKrupp Uhde GmbH filed Critical ThyssenKrupp Uhde GmbH
Priority to DE102011107959A priority Critical patent/DE102011107959A1/de
Priority to PCT/EP2012/002638 priority patent/WO2013010618A1/de
Priority to MYPI2014000157A priority patent/MY165921A/en
Priority to BR112014001110A priority patent/BR112014001110A8/pt
Priority to RU2014103495/04A priority patent/RU2553262C1/ru
Priority to CA2841089A priority patent/CA2841089A1/en
Priority to KR1020147004137A priority patent/KR20140076548A/ko
Priority to US14/233,839 priority patent/US20140212957A1/en
Priority to MX2014000655A priority patent/MX348375B/es
Priority to CN201280035474.9A priority patent/CN103781745B/zh
Priority to EP12732533.0A priority patent/EP2734488B1/de
Publication of DE102011107959A1 publication Critical patent/DE102011107959A1/de
Priority to CO14033914A priority patent/CO6890108A2/es
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C07C31/205—1,3-Propanediol; 1,2-Propanediol
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
DE102011107959A 2011-07-20 2011-07-20 Herstellung von optisch reinem Propan-1,2-diol Withdrawn DE102011107959A1 (de)

Priority Applications (12)

Application Number Priority Date Filing Date Title
DE102011107959A DE102011107959A1 (de) 2011-07-20 2011-07-20 Herstellung von optisch reinem Propan-1,2-diol
CA2841089A CA2841089A1 (en) 2011-07-20 2012-06-22 Production of optically pure propane-1,2-diol
MYPI2014000157A MY165921A (en) 2011-07-20 2012-06-22 Production of optically pure propane-1,2-diol
BR112014001110A BR112014001110A8 (pt) 2011-07-20 2012-06-22 Produção de propano-1,2-diol opticamente puro
RU2014103495/04A RU2553262C1 (ru) 2011-07-20 2012-06-22 Получение оптически чистого пропан-1,2-диола
PCT/EP2012/002638 WO2013010618A1 (de) 2011-07-20 2012-06-22 Herstellung von optisch reinem propan-1,2-diol
KR1020147004137A KR20140076548A (ko) 2011-07-20 2012-06-22 광학적으로 순수한 프로판-1,2-디올의 제조
US14/233,839 US20140212957A1 (en) 2011-07-20 2012-06-22 Production of optically pure propane-1,2-diol
MX2014000655A MX348375B (es) 2011-07-20 2012-06-22 Produccion de propan-1,2-diol opticamente puro.
CN201280035474.9A CN103781745B (zh) 2011-07-20 2012-06-22 光学纯的丙烷-1,2-二醇的生产
EP12732533.0A EP2734488B1 (de) 2011-07-20 2012-06-22 Herstellung von optisch reinem propan-1,2-diol
CO14033914A CO6890108A2 (es) 2011-07-20 2014-02-18 Producción de propano-1,2-diol ópticamente puro

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102011107959A DE102011107959A1 (de) 2011-07-20 2011-07-20 Herstellung von optisch reinem Propan-1,2-diol

Publications (1)

Publication Number Publication Date
DE102011107959A1 true DE102011107959A1 (de) 2013-01-24

Family

ID=46458423

Family Applications (1)

Application Number Title Priority Date Filing Date
DE102011107959A Withdrawn DE102011107959A1 (de) 2011-07-20 2011-07-20 Herstellung von optisch reinem Propan-1,2-diol

Country Status (12)

Country Link
US (1) US20140212957A1 (ko)
EP (1) EP2734488B1 (ko)
KR (1) KR20140076548A (ko)
CN (1) CN103781745B (ko)
BR (1) BR112014001110A8 (ko)
CA (1) CA2841089A1 (ko)
CO (1) CO6890108A2 (ko)
DE (1) DE102011107959A1 (ko)
MX (1) MX348375B (ko)
MY (1) MY165921A (ko)
RU (1) RU2553262C1 (ko)
WO (1) WO2013010618A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10138186B2 (en) * 2014-11-18 2018-11-27 Archer Daniels Midland Company Process for making biobased propylene glycol from lactic acid esters
CN110256203B (zh) * 2019-06-05 2022-06-14 江苏扬农化工集团有限公司 一种环氧丙烷废水中缩合醇醚资源化利用的方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005023737A1 (en) 2003-09-11 2005-03-17 Avecia Pharmaceuticals Limited Process for the hydrogenation of esters of alpha-substituted carboxylic acids
WO2006124899A2 (en) 2005-05-13 2006-11-23 Cargill, Incorporated Production of derivatives of lactide, production of lactides, and use of lactide in foods and to produce polymers
EP1970360A1 (en) 2007-03-16 2008-09-17 Takasago International Corporation Method for producing alcohols
WO2009103682A1 (en) 2008-02-21 2009-08-27 Nordbiochem OÜ The catalyst and method of catalytic reduction of esters of hydroxycarboxylic acid to glycols
EP2161251A1 (en) 2008-09-09 2010-03-10 Takasago International Corporation Alcohol production method by reducing ester or lactone with hydrogen
WO2011036189A2 (en) 2009-09-22 2011-03-31 Springhill S.A. The catalyst and method of catalytic hydrogenation of hydroxycarboxylic acid esters to glycols

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100644165B1 (ko) * 2002-03-14 2006-11-10 학교법인 포항공과대학교 아미노시클로펜타디에닐 루테늄 촉매를 이용한 키랄화합물 분할 방법
KR20040099348A (ko) * 2002-03-22 2004-11-26 다우 글로벌 테크놀로지스 인크. 프로필렌 글리콜 알킬 (또는 아릴) 에테르 및 에테르아세테이트의 효소적 분할
EP2141142B1 (en) * 2007-04-03 2015-03-04 Takasago International Corporation Method for producing alcohol by hydrogenating lactone or carboxylic acid ester in liquid phase

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005023737A1 (en) 2003-09-11 2005-03-17 Avecia Pharmaceuticals Limited Process for the hydrogenation of esters of alpha-substituted carboxylic acids
WO2006124899A2 (en) 2005-05-13 2006-11-23 Cargill, Incorporated Production of derivatives of lactide, production of lactides, and use of lactide in foods and to produce polymers
EP1970360A1 (en) 2007-03-16 2008-09-17 Takasago International Corporation Method for producing alcohols
WO2009103682A1 (en) 2008-02-21 2009-08-27 Nordbiochem OÜ The catalyst and method of catalytic reduction of esters of hydroxycarboxylic acid to glycols
EP2161251A1 (en) 2008-09-09 2010-03-10 Takasago International Corporation Alcohol production method by reducing ester or lactone with hydrogen
WO2011036189A2 (en) 2009-09-22 2011-03-31 Springhill S.A. The catalyst and method of catalytic hydrogenation of hydroxycarboxylic acid esters to glycols

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
BOGAR, K. [et al.]: Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol. In: Beilstein Journal of Organic Chemistry, Vol. 3, 2007, No. 50, S. 1-4. - ISSN 1860-5397 *
BOGAR, K. [et al.]: Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol. In: Beilstein Journal of Organic Chemistry, Vol. 3, 2007, No. 50, S. 1-4. – ISSN 1860-5397
G. Luo et al, Appl. Catal., A: General 2007, 332, 79-88
G. Luo et al, J. Mol. Catal. A: Chemical 2005, 230, 69-77 und G. Luo et al, Appl. Catal., A: General 2004, 275, 95-102
G.-Y. Fan et al, Chem. Lett. 2008, 37, 852-853
H. Adkins et al, J. Am. Chem, Soc. 1948, 70, 3121-3125
http://de.wikipedia.org/wiki/Optische_Reinheit *
K. Bogar et al, Beilstein J. Org. Chem 2007, 3 (50)
K. Folkers et al, J. Am. Chem. Soc. 1932, 54, 1145-1154
M. Studer et al, Adv. Synth. Catal. 2001, 343, 802-808
Petursson, S.:Highly regioselective primary etherification of racemic propane-1,2-diol bythe tin(II) bromide-catalyzed reaction with diazo[bis(4-methoxyphenyl)] methane and the resolution of enantiomers with the helpof Pseudomonas cepacia lipase. In: Tetrahedron: Asymmetry, Vol. 20, 2009, S. 887-891. -ISSN 0957-4166 *
Petursson, S.:Highly regioselective primary etherification of racemic propane-1,2-diol bythe tin(II) bromide-catalyzed reaction with diazo[bis(4-methoxyphenyl)] methane and the resolution of enantiomers with the helpof Pseudomonas cepacia lipase. In: Tetrahedron: Asymmetry, Vol. 20, 2009, S. 887–891. -ISSN 0957-4166
R. M. Painter et al, Angew. Chem. Int. Ed. 2010, 49, 9456-9459
Römpp Online, Stichwort "Racemattrennung" *
STUDER, M. [et al.]: Catalytic hydrogenation of chiral alpha-amino and alpha-hydroxy esters at room temperature with Nishimura catalyst without racemization. In: Advanced Synthesis and Catalysis, Vol. 343, 2001, S. 802-808. - ISSN 1615-4150 *
STUDER, M. [et al.]: Catalytic hydrogenation of chiral α-amino and α-hydroxy esters at room temperature with Nishimura catalyst without racemization. In: Advanced Synthesis and Catalysis, Vol. 343, 2001, S. 802-808. - ISSN 1615-4150
T. W. Green et al, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999
W. Kuriyama et al, Adv. Synth. Catal. 2010, 352, 92-96

Also Published As

Publication number Publication date
CO6890108A2 (es) 2014-03-10
EP2734488B1 (de) 2016-10-05
CA2841089A1 (en) 2013-01-24
CN103781745B (zh) 2016-10-26
EP2734488A1 (de) 2014-05-28
BR112014001110A8 (pt) 2018-04-03
BR112014001110A2 (pt) 2017-02-14
US20140212957A1 (en) 2014-07-31
MX2014000655A (es) 2014-11-13
WO2013010618A1 (de) 2013-01-24
CN103781745A (zh) 2014-05-07
MY165921A (en) 2018-05-18
RU2553262C1 (ru) 2015-06-10
MX348375B (es) 2017-05-15
KR20140076548A (ko) 2014-06-20

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R012 Request for examination validly filed
R081 Change of applicant/patentee

Owner name: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG, DE

Free format text: FORMER OWNER: UHDE GMBH, 44141 DORTMUND, DE

Effective date: 20111209

Owner name: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG, DE

Free format text: FORMER OWNER: THYSSENKRUPP UHDE GMBH, 44141 DORTMUND, DE

Effective date: 20141027

R002 Refusal decision in examination/registration proceedings
R119 Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee